Triphenylphosphine → methyl-2-[(2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxypyridine-5-carboxylate

HRID 354416Notes

Reaction equation

HRID 354416 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:10][C@H:9]1[CH2:24][OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:27]1[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][N:28]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:36][O:35][C:33]([C:30]1[CH:31]=[CH:32][C:27]([O:25][CH2:24][C@@H:9]2[CH2:10][C@H:11]([O:13][C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)[CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:28][CH:29]=1)=[O:34]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67405321(2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanolHCID 178498304HCID 178498304, compound

Product 1

HCID 69334737methyl-2-[(2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxypyridine-5-carboxylateYield 25.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanol (484 mg, 1.41 mmol), methyl 2-hydroxy-5-pyridinecarboxylate (216 mg, 1.41 mmol) and PPh3 (370 mg, 1.41 mmol) in THF (15 ml) was added DIAD (0.28 ml, 1.41 mmol) at room temperature under an atmosphere of nitrogen. The mixture was stirred over night. After removal of the solvent, the resulting residue was chromatographed on silica gel [50 g, n-hexane/EtOAc(2/1)], to give methyl-2-[(2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxypyridine-5-carboxylate (170 mg, 25%) as a colorless oil. 1H-NMR (CDCl3) δ1.47 (s, 9H), 2.37 (m, 1H), 2.46 (d, J=14.2 Hz, 1H), 3.71-4.00 (m, 2H), 3.89 (s, 3H), 4.30-4.56 (m, 2H), 4.74 (dd, J=9.8, 4.6 Hz, 1H), 5.06 (br, 1H), 6.70 (d, J=8.8 Hz, 2H), 7.05-7.09 (m, 2H), 7.33 (t, J=6.9 Hz, 1H), 7.42 (t, J=6.9 Hz, 1H), 7.67-7.75 (m, 3H), 8.09 (d, J=8.8 Hz, 1H), 8.77 (d, J=2.2 Hz, 1H).

Workup

  1. customAfter removal of the solvent
  2. customthe resulting residue was chromatographed on silica gel [50 g, n-hexane/EtOAc(2/1)]

Sources & evidence

ORD record
ord-372527c58e8946f18d2e77eb8ea63799
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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